CA2264023C - Process for producing polyamides from aminonitriles - Google Patents
Process for producing polyamides from aminonitriles Download PDFInfo
- Publication number
- CA2264023C CA2264023C CA002264023A CA2264023A CA2264023C CA 2264023 C CA2264023 C CA 2264023C CA 002264023 A CA002264023 A CA 002264023A CA 2264023 A CA2264023 A CA 2264023A CA 2264023 C CA2264023 C CA 2264023C
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- liquid
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- solid phase
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- 125000005219 aminonitrile group Chemical group 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000004952 Polyamide Substances 0.000 title claims abstract description 27
- 229920002647 polyamide Polymers 0.000 title claims abstract description 27
- 239000007790 solid phase Substances 0.000 claims abstract description 94
- 239000000203 mixture Substances 0.000 claims abstract description 86
- 239000007788 liquid Substances 0.000 claims abstract description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000007791 liquid phase Substances 0.000 claims abstract description 43
- 239000011541 reaction mixture Substances 0.000 claims abstract description 22
- 239000007792 gaseous phase Substances 0.000 claims abstract description 20
- 239000007787 solid Substances 0.000 claims abstract description 10
- 239000012071 phase Substances 0.000 claims description 44
- 239000007789 gas Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002560 nitrile group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 150000003951 lactams Chemical class 0.000 claims description 2
- 239000008247 solid mixture Substances 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- 150000001735 carboxylic acids Chemical class 0.000 description 15
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 10
- 238000002156 mixing Methods 0.000 description 9
- -1 aminoalkyl nitrile Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000002843 carboxylic acid group Chemical group 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 5
- 229960000250 adipic acid Drugs 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229940116353 sebacic acid Drugs 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000001174 ascending effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 230000005501 phase interface Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- XAUQWYHSQICPAZ-UHFFFAOYSA-N 10-amino-decanoic acid Chemical compound NCCCCCCCCCC(O)=O XAUQWYHSQICPAZ-UHFFFAOYSA-N 0.000 description 1
- VJHDPVWEDUCKRQ-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O.NCCCCCCCCCCCC(O)=O VJHDPVWEDUCKRQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 description 1
- UQXNEWQGGVUVQA-UHFFFAOYSA-N 8-aminooctanoic acid Chemical compound NCCCCCCCC(O)=O UQXNEWQGGVUVQA-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241001602688 Pama Species 0.000 description 1
- 229910052774 Proactinium Inorganic materials 0.000 description 1
- KWMYJGSOKLIBMW-UHFFFAOYSA-N acridine-1,3,6,8-tetracarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC2=NC3=CC(C(=O)O)=CC(C(O)=O)=C3C=C21 KWMYJGSOKLIBMW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960002255 azelaic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- DFJYZCUIKPGCSG-UHFFFAOYSA-N decanedinitrile Chemical compound N#CCCCCCCCCC#N DFJYZCUIKPGCSG-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- AVQYXBDAZWIFTO-UHFFFAOYSA-N dodecanedinitrile Chemical compound N#CCCCCCCCCCCC#N AVQYXBDAZWIFTO-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- LLEVMYXEJUDBTA-UHFFFAOYSA-N heptanedinitrile Chemical compound N#CCCCCCC#N LLEVMYXEJUDBTA-UHFFFAOYSA-N 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- BTNXBLUGMAMSSH-UHFFFAOYSA-N octanedinitrile Chemical compound N#CCCCCCCC#N BTNXBLUGMAMSSH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- PBLZLIFKVPJDCO-UHFFFAOYSA-N omega-Aminododecanoic acid Natural products NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910001380 potassium hypophosphite Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- ISIQQQYKUPBYSL-UHFFFAOYSA-N undecanedinitrile Chemical compound N#CCCCCCCCCCC#N ISIQQQYKUPBYSL-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/04—Preparatory processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, polyamines and polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19635077.8 | 1996-08-30 | ||
| DE19635077A DE19635077A1 (de) | 1996-08-30 | 1996-08-30 | Verfahren zur kontinuierlichen Herstellung von Polyamiden aus omega-Aminoalkylnitrilen |
| DE19709390.6 | 1997-03-07 | ||
| DE1997109390 DE19709390A1 (de) | 1997-03-07 | 1997-03-07 | Verfahren zur Herstellung von Polyamiden aus Aminonitrilen |
| PCT/EP1997/004640 WO1998008889A2 (de) | 1996-08-30 | 1997-08-26 | Verfahren zur herstellung von polyamiden aus aminonitrilen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2264023A1 CA2264023A1 (en) | 1998-03-05 |
| CA2264023C true CA2264023C (en) | 2007-03-27 |
Family
ID=26028873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002264023A Expired - Fee Related CA2264023C (en) | 1996-08-30 | 1997-08-26 | Process for producing polyamides from aminonitriles |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6194538B1 (cs) |
| EP (1) | EP0922065B1 (cs) |
| JP (1) | JP3948754B2 (cs) |
| KR (1) | KR100539338B1 (cs) |
| CN (1) | CN1128833C (cs) |
| AR (1) | AR009473A1 (cs) |
| BR (1) | BR9711257A (cs) |
| CA (1) | CA2264023C (cs) |
| CO (1) | CO4870784A1 (cs) |
| CZ (1) | CZ293844B6 (cs) |
| DE (1) | DE59708777D1 (cs) |
| ES (1) | ES2187826T3 (cs) |
| ID (1) | ID18204A (cs) |
| MY (1) | MY119018A (cs) |
| TR (1) | TR199900422T2 (cs) |
| TW (1) | TW399072B (cs) |
| WO (1) | WO1998008889A2 (cs) |
Families Citing this family (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19804023A1 (de) * | 1998-02-02 | 1999-08-05 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von Polyamiden aus Aminonitrilen |
| DE19804020A1 (de) * | 1998-02-02 | 1999-08-05 | Basf Ag | Verfahren zur Herstellung von Polyamiden aus Aminonitrilen |
| DE19804033A1 (de) * | 1998-02-02 | 1999-08-05 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von Polyamiden aus Aminonitrilen |
| DE19808490A1 (de) * | 1998-02-27 | 1999-09-02 | Basf Ag | Verfahren zur Herstellung von Polyamiden aus Aminocarbonsäureverbindungen |
| DE19808407A1 (de) * | 1998-02-27 | 1999-09-09 | Basf Ag | Herstellung von Polyamiden durch Reaktivdestillation |
| DE19808489A1 (de) * | 1998-02-27 | 1999-09-02 | Basf Ag | Verfahren zur Herstellung von Polymermischungen aus Aminonitrilen und thermoplastischen Polymeren |
| US6069228A (en) * | 1998-08-17 | 2000-05-30 | E. I. Du Pont De Nemours And Company | Process for preparing polyamides |
| DE19846014A1 (de) * | 1998-10-06 | 2000-04-13 | Basf Ag | Beschleuniger für die Herstellung von Polyamiden aus Aminonitrilen |
| ID28447A (id) * | 1998-10-26 | 2001-05-24 | Du Pont | Proses polimerisasi kontinu pembuatan poliamida-poliamida dari omega-aminonitril |
| US6075117A (en) * | 1998-12-21 | 2000-06-13 | E.I. Dupont De Nemours & Company | Process for the hydrolysis of adiponitrile and the production of nylon 6,6 using dicarboxylic acids as the sole catalyst |
| US6084056A (en) * | 1998-12-22 | 2000-07-04 | E. I. Dupont De Nemours & Company | Process for the hydrolysis of adiponitrile and the production of nylon 6,6 utilizing low catalyst levels |
| US6103863A (en) * | 1998-12-22 | 2000-08-15 | E. I. Dupont De Nemours & Company | Process for preparation of polyamide from dinitrile and diamine |
| DE19859929A1 (de) * | 1998-12-23 | 2000-06-29 | Bayer Ag | Verfahren zur Herstellung von verzweigten Polyamiden |
| DE19905754A1 (de) * | 1999-02-11 | 2000-08-17 | Basf Ag | Verfahren zur Herstellung von Polyamid 6 mit geringem Extraktgehalt, hoher Viskositätsstabilität und kleiner Remonomerisierungsrate |
| DE19935398A1 (de) * | 1999-07-30 | 2001-02-01 | Basf Ag | Verfahren zur Herstellung von Polyamiden aus Dinitrilen und Diaminen |
| DE19962573A1 (de) * | 1999-12-23 | 2001-07-05 | Basf Ag | Verfahren zur Herstellung von Polyamiden |
| US6437089B1 (en) | 2001-06-01 | 2002-08-20 | E. I. Du Pont De Nemours And Company | Process for the production of nylon 6 |
| US6472501B1 (en) * | 2001-06-01 | 2002-10-29 | E. I. Du Pont De Nemours And Company | Process for making nylon 6,6 |
| DE10217439A1 (de) * | 2002-04-18 | 2003-10-30 | Basf Ag | Verfahren zur Herstellung von Polyamiden |
| DE102004006955A1 (de) * | 2004-02-12 | 2005-09-01 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von Polyamiden |
| DE102004027022A1 (de) * | 2004-06-02 | 2006-01-05 | Basf Ag | Verfahren zur Abtrennung von Ammoniak und Wasser aus Lactam-haltigen Gemischen |
| BRPI0720299A2 (pt) | 2006-12-13 | 2014-02-04 | Basf Se | Composição de moldagem termoplástica, uso mesma, e, moldagem |
| DE102008038411A1 (de) | 2007-09-11 | 2009-03-12 | Basf Se | Flammgeschützte Polyamide |
| US8309221B2 (en) * | 2007-10-01 | 2012-11-13 | Jay Plaehn | Reinforced foam panel |
| ATE522577T1 (de) | 2007-12-18 | 2011-09-15 | Basf Se | Thermoplastische polyamide mit polyetheraminen |
| DE102009011668A1 (de) | 2008-03-05 | 2009-09-10 | Basf Se | Polyamid und hyperverzweigte Polyesster enthaltende Formmasse |
| US8119718B2 (en) | 2008-06-27 | 2012-02-21 | Basf Se | Thermally conductive polyamides with diatomaceous earth |
| CN102144001A (zh) * | 2008-07-02 | 2011-08-03 | 巴斯夫欧洲公司 | 发泡性聚酰胺 |
| DE102008058246A1 (de) | 2008-11-19 | 2010-05-20 | Basf Se | Hochmolekulare Polyamide |
| EP2379644B1 (de) | 2008-12-16 | 2018-08-22 | Basf Se | Wärmealterungsbeständige polyamide |
| EP2264093A1 (de) | 2009-06-16 | 2010-12-22 | THOR GmbH | Flammgeschützte Polyamidformmassen |
| CN102471938B (zh) | 2009-06-30 | 2014-08-13 | 巴斯夫欧洲公司 | 包含可染色颗粒的聚酰胺纤维及其生产方法 |
| WO2011000816A1 (de) | 2009-07-03 | 2011-01-06 | Basf Se | Nanokompositblends enthaltend polyamide und polyolefine |
| WO2011009798A1 (de) | 2009-07-21 | 2011-01-27 | Basf Se | Nanokompositblends auf basis von polyamiden und polyarylenethersulfonen |
| WO2011009877A1 (de) | 2009-07-24 | 2011-01-27 | Basf Se | Flammgeschützte polyamidformmassen |
| DK2493968T3 (en) | 2009-10-27 | 2015-03-02 | Basf Se | Heat stabilized polyamide composition |
| CA2778491A1 (en) | 2009-10-27 | 2011-05-05 | Basf Se | Heat aging-resistant polyamides with flame retardancy |
| WO2011069942A1 (de) | 2009-12-08 | 2011-06-16 | Basf Se | Teilaromatische copolyamidformmassen auf der basis von octamethylendiamin |
| CN102803387B (zh) | 2009-12-09 | 2014-06-25 | 巴斯夫欧洲公司 | 半芳族、半结晶共聚酰胺 |
| DE102010062886A1 (de) | 2009-12-16 | 2011-06-22 | Basf Se, 67063 | Polyarylenethersulfone als Schlagzähmodifier |
| US8466221B2 (en) * | 2010-03-09 | 2013-06-18 | Basf Se | Polyamides that resist heat-aging |
| RU2566148C2 (ru) | 2010-03-09 | 2015-10-20 | Басф Се | Полиамиды, устойчивые к тепловому старению |
| WO2011134930A1 (de) | 2010-04-30 | 2011-11-03 | Basf Se | Langfaserverstärkte polyamide mit polyolefinen |
| DE102010023770A1 (de) | 2010-06-15 | 2011-12-15 | Basf Se | Glühdrahtbeständige Formmassen |
| MY156769A (en) | 2010-06-15 | 2016-03-31 | Basf Se | Heat-aging-resistant polyamides |
| US8563680B2 (en) | 2010-06-15 | 2013-10-22 | Basf Se | Heat-aging-resistant polyamides |
| WO2012013564A1 (de) | 2010-07-30 | 2012-02-02 | Basf Se | Flammgeschützte formmassen |
| EP2415827A1 (de) | 2010-08-04 | 2012-02-08 | Basf Se | Flammgeschützte Polyamide mit Schichtsilikaten |
| WO2012062594A1 (de) | 2010-11-11 | 2012-05-18 | Basf Se | Wärmealterungsbeständige polyamide |
| ES2555128T3 (es) | 2010-11-18 | 2015-12-29 | Styrolution Europe Gmbh | Masas de moldeo termoplásticas a base de copolímeros de estireno y poliamidas; procedimiento para su producción y su utilización |
| JP5940087B2 (ja) | 2010-12-16 | 2016-06-29 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 耐グローワイヤ性ポリアミド |
| US8575295B2 (en) | 2010-12-16 | 2013-11-05 | Basf Se | Glow-wire resistant polyamides |
| WO2012084785A1 (de) | 2010-12-20 | 2012-06-28 | Basf Se | Thermoplastische formmassen auf basis von styrol-copolymeren und polyamiden mit verbesserter tieftemperaturzähigkeit |
| KR101869999B1 (ko) | 2011-01-18 | 2018-06-22 | 바스프 에스이 | 가수분해-안정성 폴리아미드 |
| US8629220B2 (en) | 2011-01-18 | 2014-01-14 | Basf Se | Hydrolysis-resistant polyamides |
| US8629206B2 (en) | 2011-01-20 | 2014-01-14 | Basf Se | Flame-retardant thermoplastic molding composition |
| WO2012143316A1 (de) | 2011-04-21 | 2012-10-26 | Basf Se | Vorrichtung zur befestigung von wärmeträgerleitungen an einem behälter |
| EP2702102A1 (de) | 2011-04-28 | 2014-03-05 | Basf Se | Flammgeschütze formmassen |
| US8653168B2 (en) | 2011-05-10 | 2014-02-18 | Basf Se | Flame-retardant thermoplastic molding composition |
| EP2527402A1 (de) | 2011-05-27 | 2012-11-28 | Basf Se | Thermoplastische Formmasse |
| US8987357B2 (en) | 2011-05-27 | 2015-03-24 | Basf Se | Thermoplastic molding composition |
| DE102011104303A1 (de) | 2011-06-03 | 2012-12-06 | Basf Se | Photovoltaik-System zur Installation auf Dächern mit Kunststoffträger und Photovoltaik-Modul |
| US8883904B2 (en) | 2011-09-15 | 2014-11-11 | Basf Se | Mixtures of silver and zinc oxide as stabilizer for flame-retardant polyamides |
| JP6049730B2 (ja) | 2011-09-15 | 2016-12-21 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 赤リン含有難燃性ポリアミド用の安定剤としての銀／酸化亜鉛混合物 |
| EP2573138A1 (de) | 2011-09-21 | 2013-03-27 | Basf Se | Polyamid-Formmassen |
| JP6124910B2 (ja) | 2011-11-25 | 2017-05-10 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ブロー成形可能なポリアミド成形材料 |
| WO2013083508A1 (de) | 2011-12-07 | 2013-06-13 | Basf Se | Flammgeschützte polyamide mit flüssigkristallinen polyestern |
| AU2013224359A1 (en) | 2012-02-20 | 2014-09-04 | Basf Se | CuO/ZnO compounds as stabilisers for flame retardant polyamides |
| EP2641939A1 (de) | 2012-03-21 | 2013-09-25 | Basf Se | Hellgefärbte flammgeschützte Polyamide |
| EP2650331A1 (de) | 2012-04-11 | 2013-10-16 | Basf Se | Polyamide für Trinkwasseranwendungen |
| KR102021635B1 (ko) | 2012-06-18 | 2019-10-15 | 바스프 에스이 | 폴리아크릴로니트릴 단독중합체를 갖는 난연성 폴리아미드 |
| EP2898009B1 (de) | 2012-09-19 | 2016-10-12 | Basf Se | Flammgeschützte polyamide mit heller farbe |
| JP6509195B2 (ja) | 2013-04-15 | 2019-05-08 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 耐グローワイヤ性ポリアミド |
| DE102014215370A1 (de) | 2013-09-05 | 2015-03-05 | Basf Se | Langfaserverstärkte flammgeschützte Polyamide |
| GB201421293D0 (en) | 2014-12-01 | 2015-01-14 | Xeros Ltd | New cleaning method, apparatus and use |
| WO2016087324A1 (de) | 2014-12-01 | 2016-06-09 | Basf Se | Flammgeschützte polyamide mit sulfonsäuresalzen |
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| US11674015B2 (en) | 2015-04-16 | 2023-06-13 | Basf Se | Polyamides with improved optical properties |
| US10669394B2 (en) | 2015-06-19 | 2020-06-02 | Basf Se | Polyamide compositions with high melt flow and good mechanical properties |
| EP3118247A1 (de) | 2015-07-15 | 2017-01-18 | Basf Se | Polyamide mit besseren optischen eigenschaften |
| EP3130633A1 (de) | 2015-08-13 | 2017-02-15 | Basf Se | Polyamide mit guter mechanik und schwindung |
| EP3135730A1 (de) | 2015-08-27 | 2017-03-01 | Basf Se | Polyamide mit niedrigem kristallisationspunkt und geringer schwindung |
| EP3448916B1 (en) | 2016-04-26 | 2020-10-14 | Basf Se | Thermoplastic polyamide particles |
| CN109328208B (zh) | 2016-06-15 | 2021-08-27 | 巴斯夫欧洲公司 | 多元醇中的聚酰胺分散体及其制备 |
| EP3472244B1 (de) | 2016-06-15 | 2021-08-11 | Basf Se | Schlagzähmodifier basierend auf polyisobuten für polyamide |
| BR112019006385B1 (pt) | 2016-10-13 | 2023-03-28 | Basf Se | Composição de modelagem termoplástica, uso da dita composição e modelagem de qualquer tipo |
| JP7114608B2 (ja) | 2017-02-01 | 2022-08-08 | ビーエーエスエフ ソシエタス・ヨーロピア | ナフタル酸無水物末端基を含むポリアリーレンエーテルスルホン |
| KR102524256B1 (ko) | 2017-03-01 | 2023-04-20 | 바스프 에스이 | 난연성 pvp 함유 폴리아미드 |
| KR102634718B1 (ko) | 2017-06-22 | 2024-02-07 | 바스프 에스이 | 인 및 Al-포스포네이트를 갖는 폴리아미드 |
| BR112020019990B1 (pt) | 2018-04-13 | 2023-11-28 | Basf Se | Composição de modelagem termoplástica, processo de produção de uma composição de modelagem termoplástica, uso da composição de modelagem termoplástica, fibra e processo de produção |
| WO2020035455A1 (en) | 2018-08-16 | 2020-02-20 | Basf Se | Thermoplastic molding material |
| JP7612594B2 (ja) | 2019-02-20 | 2025-01-14 | ビーエーエスエフ ソシエタス・ヨーロピア | 熱可塑性成形化合物 |
| CN113474402B (zh) | 2019-02-25 | 2023-10-27 | 巴斯夫欧洲公司 | 热塑性模塑组合物 |
| CN114341266A (zh) | 2019-09-05 | 2022-04-12 | 巴斯夫欧洲公司 | 耐热的热塑性模塑组合物 |
| EP3808810B1 (de) | 2019-10-16 | 2023-03-29 | INEOS Styrolution Group GmbH | Thermoplastische formmassen für rotomolding-verfahren |
| KR20220134581A (ko) | 2020-01-27 | 2022-10-05 | 바스프 에스이 | 열에 내성인 열가소성 폴리아미드 성형 조성물 |
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| US20230203304A1 (en) | 2020-03-20 | 2023-06-29 | Basf Se | Plasticized polyamide molding compositions |
| WO2021191209A1 (en) | 2020-03-25 | 2021-09-30 | Basf Se | Heat-aging resistant polyamide molding compositions |
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| US20240262043A1 (en) | 2021-05-11 | 2024-08-08 | Basf Se | Laser-inscribed and laser-welded shaped bodies and production thereof |
| BR112023025307A2 (pt) | 2021-06-04 | 2024-02-27 | Basf Se | Composição de moldagem termoplástica, processo para produzir um material de moldagem termoplástico, uso do material de moldagem termoplástico, artigo moldado ou extrudado, processo para produzir artigos moldados ou extrudados e uso de copolímeros em bloco de poliamida-poliéter |
| JP2025521224A (ja) | 2022-06-08 | 2025-07-08 | ビーエーエスエフ ソシエタス・ヨーロピア | ポリアミド化合物を製造するためのリサイクル方法 |
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|---|---|---|---|---|
| US2245129A (en) * | 1935-01-02 | 1941-06-10 | Du Pont | Process for preparing linear polyamides |
| CA1186444A (en) | 1981-05-18 | 1985-04-30 | Hansdieter Hofmann | Method for producing spinnable polyamides, etc. |
| US4568736A (en) * | 1984-09-17 | 1986-02-04 | The Standard Oil Company | Preparation of polyamide from omega-aminonitrile with oxygen containing phosphorus catalyst |
| DE3534817A1 (de) * | 1985-09-30 | 1987-04-02 | Davy Mckee Ag | Verfahren zur herstellung von polyamid |
| US5310827A (en) * | 1987-01-22 | 1994-05-10 | Kuraray Co., Ltd. | Polyamide copolymers |
| US5109104A (en) * | 1990-10-04 | 1992-04-28 | E. I. Du Pont De Nemours And Company | Preparation of polyamides from omega-aminonitriles |
| US5185427A (en) * | 1991-08-20 | 1993-02-09 | E. I. Du Pont De Nemours And Company | Process for the production of copolyamides from amino nitrile, diamine and dicarboxylic acid |
| DE4430480A1 (de) * | 1994-08-27 | 1996-02-29 | Basf Ag | Hochmolekulare Polyamide aus Nitrilen |
| FR2735471B1 (fr) * | 1995-06-16 | 1997-08-22 | Rhone Poulenc Chimie | Procede de preparation de lactames |
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1997
- 1997-08-26 CZ CZ1999675A patent/CZ293844B6/cs not_active IP Right Cessation
- 1997-08-26 TR TR1999/00422T patent/TR199900422T2/xx unknown
- 1997-08-26 EP EP97944794A patent/EP0922065B1/de not_active Expired - Lifetime
- 1997-08-26 WO PCT/EP1997/004640 patent/WO1998008889A2/de active IP Right Grant
- 1997-08-26 CA CA002264023A patent/CA2264023C/en not_active Expired - Fee Related
- 1997-08-26 DE DE59708777T patent/DE59708777D1/de not_active Expired - Lifetime
- 1997-08-26 US US09/242,714 patent/US6194538B1/en not_active Expired - Lifetime
- 1997-08-26 CN CN97199224A patent/CN1128833C/zh not_active Expired - Fee Related
- 1997-08-26 ES ES97944794T patent/ES2187826T3/es not_active Expired - Lifetime
- 1997-08-26 BR BR9711257A patent/BR9711257A/pt not_active IP Right Cessation
- 1997-08-26 JP JP51127398A patent/JP3948754B2/ja not_active Expired - Fee Related
- 1997-08-26 KR KR10-1999-7001738A patent/KR100539338B1/ko not_active Expired - Fee Related
- 1997-08-27 TW TW086112321A patent/TW399072B/zh not_active IP Right Cessation
- 1997-08-28 AR ARP970103929A patent/AR009473A1/es active IP Right Grant
- 1997-08-29 MY MYPI97004011A patent/MY119018A/en unknown
- 1997-08-29 CO CO97050221A patent/CO4870784A1/es unknown
- 1997-09-01 ID IDP973048A patent/ID18204A/id unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR100539338B1 (ko) | 2005-12-28 |
| CZ293844B6 (cs) | 2004-08-18 |
| AR009473A1 (es) | 2000-04-26 |
| JP3948754B2 (ja) | 2007-07-25 |
| JP2000516977A (ja) | 2000-12-19 |
| TW399072B (en) | 2000-07-21 |
| MY119018A (en) | 2005-03-31 |
| DE59708777D1 (de) | 2003-01-02 |
| CA2264023A1 (en) | 1998-03-05 |
| CN1235621A (zh) | 1999-11-17 |
| ES2187826T3 (es) | 2003-06-16 |
| CN1128833C (zh) | 2003-11-26 |
| TR199900422T2 (xx) | 1999-04-21 |
| EP0922065B1 (de) | 2002-11-20 |
| KR20000035962A (ko) | 2000-06-26 |
| ID18204A (id) | 1998-03-12 |
| BR9711257A (pt) | 1999-08-17 |
| WO1998008889A2 (de) | 1998-03-05 |
| CZ67599A3 (cs) | 1999-06-16 |
| US6194538B1 (en) | 2001-02-27 |
| CO4870784A1 (es) | 1999-12-27 |
| WO1998008889A3 (de) | 1998-06-25 |
| EP0922065A2 (de) | 1999-06-16 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |